GTM 108: From CPA to CRO - Lessons from a 25-Year Software Sales Career with Matt Breslin

As Upland's Chief Revenue Officer, Matt Breslin oversees customer success, demand generation and communications, sales, revenue enablement, and revenue analysis, supporting our Shared Services Organization. Matt has 25 years of experience in the software industry, most recently leading a $700 million business at Infor. Prior to that, he held senior leadership positions at SAP and Oracle, driving incredible results across the board. Matt started his career as a Certified Public Accountant for Price Waterhouse and Kraft Foods.Discussed in this Episode:The importance of avoiding blind spots in the sales process and aligning the sales process with the customer's business pains and processes.Lessons learned from closing a multi-million dollar deal early in his career, including the value of attention to detail and building strong customer relationships.The benefits of focusing sales teams on specific sales motions, such as new logo acquisition or account expansion.Highlights:(14:10) Challenging the belief that 3-5X pipeline coverage is the answer to sales problems.(18:44) The story of driving to a customer's child's soccer game to close a multi-million dollar deal.(26:01) The biggest surprise when transitioning from an individual contributor to a leader.(41:06) The importance of aligning sales teams to the right motions.(44:16) One thing revenue leaders believe to be true that Matt thinks is bull$***.(45:23) One thing that is working for Matt in go-to-market right now.Guest Speaker (Matt Breslin):LinkedIn: https://www.linkedin.com/in/matt-breslin-09a4354/Sponsors:Brought to you by Apollo. Ever wonder what automating your entire outbound workflow could do for your revenue team? Apollo.io brings this to life by centralizing your entire go-to-market execution in one platform. Sellers using automation in their outbound efforts see a 70% increase in open rates and 4x more meetings booked while saving hours on manual, tedious tasks. Brought to you by Vanta. Your deal is almost closed, and all that’s left is the security review. But when it comes to those lengthy security questionnaires, the endless back and forths can often cause deals to stall out, leaving your deal at risk and dollars on the table. With Vanta Questionnaire Automation, GTM teams can complete security reviews up to 5X faster. Over 8,000 global companies use Vanta to streamline security questionnaires and close deals fast. Register for an upcoming webinar with live Q&A here. Brought to you by IPS. Most recruiting firms fill an order, but IPS is a different breed of search firm. They dig into your business to understand its current state and the future vision and are relentlessly in pursuit of the very best leaders, sales people, marketers, and engineering talent out there. The GTMnow Podcast The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.Visit gtmnow.com for more episodes and other interesting content.